ZA200503460B - 1,2,4-thiadiazole compounds and arthropod controlling composition containing the same - Google Patents
1,2,4-thiadiazole compounds and arthropod controlling composition containing the same Download PDFInfo
- Publication number
- ZA200503460B ZA200503460B ZA200503460A ZA200503460A ZA200503460B ZA 200503460 B ZA200503460 B ZA 200503460B ZA 200503460 A ZA200503460 A ZA 200503460A ZA 200503460 A ZA200503460 A ZA 200503460A ZA 200503460 B ZA200503460 B ZA 200503460B
- Authority
- ZA
- South Africa
- Prior art keywords
- thiadiazole
- methyl
- compound
- formula
- substituted
- Prior art date
Links
- 241000238421 Arthropoda Species 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims description 32
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 title description 6
- -1 1,2,4-thiadiazole compound Chemical class 0.000 claims abstract description 147
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 26
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 26
- 230000001276 controlling effect Effects 0.000 claims abstract description 16
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 6
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 4
- ZHIFCCKUBDROKL-UHFFFAOYSA-N 3-but-2-ynoxy-5-(cyclohexylmethyl)-1,2,4-thiadiazole Chemical compound CC#CCOC1=NSC(CC2CCCCC2)=N1 ZHIFCCKUBDROKL-UHFFFAOYSA-N 0.000 claims description 2
- WJFHZSHKDBPWNI-UHFFFAOYSA-N 5-(2-methylcyclohexyl)-3-pent-2-ynoxy-1,2,4-thiadiazole Chemical compound CCC#CCOC1=NSC(C2C(CCCC2)C)=N1 WJFHZSHKDBPWNI-UHFFFAOYSA-N 0.000 claims description 2
- GSFBJLYSHGBCPP-UHFFFAOYSA-N 5-cyclopentyl-3-pent-2-ynoxy-1,2,4-thiadiazole Chemical compound CCC#CCOC1=NSC(C2CCCC2)=N1 GSFBJLYSHGBCPP-UHFFFAOYSA-N 0.000 claims description 2
- PVYUSZWPQGZGIH-UHFFFAOYSA-N 3-but-2-ynoxy-5-(3-ethylcyclohexyl)-1,2,4-thiadiazole Chemical compound C1C(CC)CCCC1C1=NC(OCC#CC)=NS1 PVYUSZWPQGZGIH-UHFFFAOYSA-N 0.000 claims 1
- ZJESJMHHDIOBTQ-UHFFFAOYSA-N 3-but-2-ynoxy-5-(4-methylcyclohexyl)-1,2,4-thiadiazole Chemical compound CC#CCOC1=NSC(C2CCC(C)CC2)=N1 ZJESJMHHDIOBTQ-UHFFFAOYSA-N 0.000 claims 1
- AVZKNFNRYAXSHU-UHFFFAOYSA-N 5-(3-ethylcyclohexyl)-3-pent-2-ynoxy-1,2,4-thiadiazole Chemical compound CCC#CCOC1=NSC(C2CC(CC)CCC2)=N1 AVZKNFNRYAXSHU-UHFFFAOYSA-N 0.000 claims 1
- CHBQRJADZPGBHX-UHFFFAOYSA-N 5-(cyclohexylmethyl)-3-pent-2-ynoxy-1,2,4-thiadiazole Chemical compound CCC#CCOC1=NSC(CC2CCCCC2)=N1 CHBQRJADZPGBHX-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 abstract description 4
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- 238000004519 manufacturing process Methods 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000009472 formulation Methods 0.000 description 15
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
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- NEEDEQSZOUAJMU-UHFFFAOYSA-N but-2-yn-1-ol Chemical compound CC#CCO NEEDEQSZOUAJMU-UHFFFAOYSA-N 0.000 description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 11
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- 125000000217 alkyl group Chemical group 0.000 description 7
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
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- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- SMKRKQBMYOFFMU-UHFFFAOYSA-N prallethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(CC#C)C(=O)C1 SMKRKQBMYOFFMU-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 229960005349 sulfur Drugs 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002337884 | 2002-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200503460B true ZA200503460B (en) | 2006-08-30 |
Family
ID=32321859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200503460A ZA200503460B (en) | 2002-11-21 | 2005-04-29 | 1,2,4-thiadiazole compounds and arthropod controlling composition containing the same |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7301032B2 (pt) |
| EP (1) | EP1569922B1 (pt) |
| KR (1) | KR101012547B1 (pt) |
| CN (2) | CN100408625C (pt) |
| AT (1) | ATE450519T1 (pt) |
| AU (1) | AU2003274762B2 (pt) |
| BR (1) | BR0316439A (pt) |
| DE (1) | DE60330381D1 (pt) |
| ES (1) | ES2335986T3 (pt) |
| IL (1) | IL167898A (pt) |
| MX (1) | MXPA05005336A (pt) |
| PT (1) | PT1569922E (pt) |
| TW (1) | TWI306390B (pt) |
| WO (1) | WO2004046125A1 (pt) |
| ZA (1) | ZA200503460B (pt) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0415364A (pt) * | 2003-10-15 | 2006-12-12 | Sumitomo Chemical Co | compostos de 1,2,4-tiadiazol e composições de controle de pestes contendo os mesmos |
| JP5649353B2 (ja) | 2010-07-28 | 2015-01-07 | キヤノン株式会社 | インクジェット用弾性部材 |
| CN103589106B (zh) * | 2013-10-18 | 2016-04-20 | 宁波科盛光电有限公司 | 高耐磨tpe塑芯脚轮专用料 |
| KR101773442B1 (ko) | 2017-02-15 | 2017-08-31 | 김순일 | 흡혈성 절지동물 기피제 조성물 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3030661A1 (de) | 1980-08-13 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | Hetaryl-propargylether, ihre herstellung und ihre verwendung in schaedlingsbekaempfungsmitteln, diese stoffe enthaltende schaedlingsbekaempfungsmittel, sowie ihre herstellung und verwendung |
| JPS63165376A (ja) * | 1986-12-27 | 1988-07-08 | Nippon Soda Co Ltd | オキサ（チア）ジアゾ−ル誘導体その製造方法及び殺ダニ剤 |
| DD295522A5 (de) * | 1989-07-26 | 1991-11-07 | �����@������������������k�� | 5-Alkyl-1,3,4-Thiadiazole, Verfahren zu ihrer Herstellung und Verwendung als Schädlingsbekämpfungsmittel |
| JP3604117B2 (ja) * | 1997-03-06 | 2004-12-22 | 株式会社クラレ | 熱可塑性重合体組成物 |
| JP3540920B2 (ja) * | 1997-09-29 | 2004-07-07 | 鐘淵化学工業株式会社 | 架橋可能なゴム組成物、及びその架橋ゴム |
| JP3583593B2 (ja) * | 1997-09-29 | 2004-11-04 | 鐘淵化学工業株式会社 | 架橋可能なゴム組成物、及びその架橋ゴム |
| JP2001247722A (ja) * | 2000-03-02 | 2001-09-11 | Yokohama Rubber Co Ltd:The | ゴム組成物 |
| EP1475374A4 (en) | 2002-01-17 | 2005-05-04 | Sumitomo Chemical Co | THIADIAZONE COMPOUNDS AND THEIR USE |
-
2002
- 2002-12-24 CN CNB028300742A patent/CN100408625C/zh not_active Expired - Fee Related
-
2003
- 2003-10-24 TW TW092129601A patent/TWI306390B/zh not_active IP Right Cessation
- 2003-10-28 DE DE60330381T patent/DE60330381D1/de not_active Expired - Lifetime
- 2003-10-28 WO PCT/JP2003/013750 patent/WO2004046125A1/en active Application Filing
- 2003-10-28 US US10/532,478 patent/US7301032B2/en not_active Expired - Fee Related
- 2003-10-28 ES ES03758967T patent/ES2335986T3/es not_active Expired - Lifetime
- 2003-10-28 EP EP03758967A patent/EP1569922B1/en not_active Expired - Lifetime
- 2003-10-28 MX MXPA05005336A patent/MXPA05005336A/es active IP Right Grant
- 2003-10-28 CN CNB2003801037412A patent/CN1324020C/zh not_active Expired - Fee Related
- 2003-10-28 KR KR1020057009141A patent/KR101012547B1/ko not_active IP Right Cessation
- 2003-10-28 AU AU2003274762A patent/AU2003274762B2/en not_active Ceased
- 2003-10-28 PT PT03758967T patent/PT1569922E/pt unknown
- 2003-10-28 AT AT03758967T patent/ATE450519T1/de not_active IP Right Cessation
- 2003-10-28 BR BR0316439-0A patent/BR0316439A/pt active Search and Examination
-
2005
- 2005-04-07 IL IL167898A patent/IL167898A/en not_active IP Right Cessation
- 2005-04-29 ZA ZA200503460A patent/ZA200503460B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050075443A (ko) | 2005-07-20 |
| IL167898A (en) | 2011-11-30 |
| DE60330381D1 (de) | 2010-01-14 |
| CN1324020C (zh) | 2007-07-04 |
| PT1569922E (pt) | 2010-01-22 |
| EP1569922B1 (en) | 2009-12-02 |
| WO2004046125A1 (en) | 2004-06-03 |
| ATE450519T1 (de) | 2009-12-15 |
| EP1569922A1 (en) | 2005-09-07 |
| KR101012547B1 (ko) | 2011-02-07 |
| AU2003274762A1 (en) | 2004-06-15 |
| CN100408625C (zh) | 2008-08-06 |
| US20060052422A1 (en) | 2006-03-09 |
| BR0316439A (pt) | 2005-10-11 |
| US7301032B2 (en) | 2007-11-27 |
| ES2335986T3 (es) | 2010-04-07 |
| CN1714123A (zh) | 2005-12-28 |
| MXPA05005336A (es) | 2005-07-25 |
| TW200418385A (en) | 2004-10-01 |
| TWI306390B (en) | 2009-02-21 |
| AU2003274762B2 (en) | 2009-09-17 |
| CN1714086A (zh) | 2005-12-28 |
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